Sodium Hydroxide → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylthio)pyrazolo[5,1-b][1,3]thiazole

HRID 41269ノート

反応式

HRID 41269 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[C:20]1[N:21]2[N:27]=[C:26]([S:28]([CH3:31])(=O)=O)[CH:25]=[C:22]2[S:23][CH:24]=1.[OH-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[C:20]1[N:21]2[N:27]=[C:26]([S:28][CH3:31])[CH:25]=[C:22]2[S:23][CH:24]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 582234563-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole

生成物 1

HCID 582234093-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylthio)pyrazolo[5,1-b][1,3]thiazole収率 9.3%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To tetrahydrofuran (20 mL) was added dropwise titanium tetrachloride (1.10 mL, 10.1 mmol) at −78° C., and the mixture was stirred for 10 minutes. At the same temperature, a tetrahydrofuran (20 mL) solution of lithium aluminum hydride (767 mg, 20.1 mmol) was gradually added dropwise and stirred for 30 minutes. To the mixture was added 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole (384 mg, 1.01 mmol), and the mixture was stirred at room temperature for 30 minutes. The mixture was heated at 50° C. for one hour. After the reaction was completed, 5N sodium hydroxide was gradually added dropwise while cooling on ice to stop the reaction. The reaction mixture was filtered with Celite and extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1/1) to obtain the title compound (32.8 mg, 0.094 mmol).

後処理

  1. stirringstirred for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperaturewhile cooling on ice
  4. customthe reaction
  5. filtrationThe reaction mixture was filtered with Celite
  6. extractionextracted with ethyl acetate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-4c42e7d511d04b8e9cad177ae8f1ab23
出典データセット
uspto-grants-2013_09
特許番号
US08530504B2

反応ノート

読み込み中…